Water → 2-[3,4-Dimethoxy-2-(2-phenylethyl)phenyl]-4,5-dihydro-4,4-dimethyloxazole

HRID 476671Notes

Reaction equation

HRID 476671 reaction equation
[C:1]1([CH2:7][CH2:8][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1([CH3:29])[CH2:16][O:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18]=2OC)=[N:13]1.O>O1CCCC1>[CH3:26][O:25][C:19]1[C:18]([CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:17]([C:14]2[O:15][CH2:16][C:12]([CH3:11])([CH3:29])[N:13]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 110217964,5-Dihydro 4,4-dimethyl-2-(2,3,4-trimethoxyphenyl)oxazoleHCID 178419670HCID 178419670, compound

Product 1

HCID 230438382-[3,4-Dimethoxy-2-(2-phenylethyl)phenyl]-4,5-dihydro-4,4-dimethyloxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phenylethyl magnesium bromide (1M in tetrahydrofuran (40 ml) was added to a stirred solution of 4,5-dihydro 4,4-dimethyl-2-(2,3,4-trimethoxyphenyl) oxazole (5.3 g 0.02M) in dry tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred at 20° for 16 hours. Water (200 ml) was added and the aqueous phase thoroughly extracted with diethyl ether (3×200 ml). The organic solution was dried over magnesium sulphate, filtered and evaporated to leave an oil which was purified by column chromatography on SiO2 eluting with ether/petroleum ether (50/50) to give a colorless oil (6.2 g); MS m/e 339.

Workup

  1. extractionthe aqueous phase thoroughly extracted with diethyl ether (3×200 ml)
  2. dry with materialThe organic solution was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customto leave an oil which
  6. customwas purified by column chromatography on SiO2 eluting with ether/petroleum ether (50/50)

Sources & evidence

ORD record
ord-cec43a2b75f2472794a7d2491df5e5b9
Source dataset
uspto-grants-1989_12
Patent number
US04885313

Reaction notes

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